(4-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone | 1357912-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone
• CAS: 1357912-57-2
• 化学式: C₁₇H₁₅BrO₂S
• 分子量: 363.275
• InChiKey: ZZSIDGZPSHPMJT-VYDXJSESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 1-(4-bromophenyl)-3-phenyl-2-propen-1-one 在 C₃₂H₂₈F₆N₄O₃ 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (4-bromophenyl)(4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone 、 (4-bromophenyl)((2S,3R,4R)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone 、 (4-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone
  参考文献：
  名称：

  Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes

  摘要：

  A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction efficiency was observed and a synthetically potential gram-synthesis was also conducted.

  DOI：

  10.1021/ol2034959